I Screwed Up, Here's What I learned Vol. 2

The shadows we cast as leaders, and how cold those shadows can feel

Across many years in leadership roles, I’ve had many opportunities to uplift and inspire people. This I consider the primary reward of leadership.

But the vignette which follows is not about the good moments. It’s about getting it wrong, which I have done from time to time.

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I recently reconnected with an old colleague from the Air Force. He’d been a pilot in the squadron I commanded.

Our engagement did not go well. He was angry with me and let me know about it. In the exchange which followed, I recognized why.

I’d made a really piss-poor mistake. It impacted him, and that impact still stung even after a lot of time had passed.

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About a decade ago, this pilot had asked me for a letter of recommendation. He was in the middle of a professional transition and enlisted my support.

We had not worked together for a couple years at that point, but I thought quite highly of him and earnestly wanted to help.

There were two problems though.

First, he’d had to rattle my cage repeatedly to get my attention, which was not cool.

Second, after committing to him that I would write the letter, I didn’t do it. He had asked for my email to send the materials, and I never sent it.

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This is the part in such stories where there is a natural grapple to rationalize why something happened.

I’m not going to do that. There are all kinds of circumstances that create friction and difficulty in life.

None of them are relevant.

The bottom line is that I made a commitment and did not keep it. I was negligent.

It’s unacceptable.

The guy was able to get what he needed from others and successfully navigated that part of his journey without my help.

But my failure to follow through left a mark. Over time, as he revisited the neglect of a trusted leader letting him down, that mark became a scar. Which is why, when we collided years later, he was understandably unkind.

All I could do was apologize. It was obvious that the manner in which I had left this individual hanging inflicted a degree of psychic harm.

It would have been different if we were peers. But I had been his commander. I had held myself out to the world as a “people first” leader.

He had bought into that. He had allowed himself to believe, based on what he had seen in me, that some leaders were different. That they actually cared. That they actually saw it as their duty to support and serve their teams.

Because he had looked upon me with admiration and allowed my leadership to influence his worldview, getting ghosted felt like an especially sharp cut. He felt like the joke had been on him for believing in me. This kind of wound is deep enough to pierce things like esteem and worth.

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Of course, this was all 180 degrees opposite from what I had intended.

But as I have often said when coaching and developing others, leading people requires more than good intentions.

When you have the privilege of leading people, you have to be clever and capable enough to foresee how your intentions might be nullified, twisted, or bombed on the runway.

What you intend doesn’t matter. Only how you ultimately make others feel.

In this case, I made a commitment I had intended to keep without recognizing how that intent might get disrupted.

Part of why that happened involves my underestimation of how my failure would impact someone else, and how much it would mean to them. This led to mis-prioritizing and eventually dropping an important ball.

Leaders often under-estimate the size of the shadow they cast.

They under-appreciate how cold those shadows can be when they let people down.

They underestimate the power of their words. And especially the deafening signals transmitted by their actions, or inactions.

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I didn’t just needlessly scorch a relationship with someone I held in high regard Likely, I also damaged that person’s ability to trust and believe in other leaders.

I share this so you can learn from my mistake.

Whatever your stage of development, understand the power and danger of commitments. Powerful in relationship building when you keep them. A blowtorch on the connective tissue of a relationship when you don’t.

And if you take away nothing else, remember that the more senior your role and position, the greater your power to uplift. But also, the greater your power to damage others, whether you intend to or not.

As a senior leader, you are a major figure in the lives of others. If you’re not OK with that, choose another profession.

As a senior leader, you have the unique capability to contribute to decline or ascendancy in others. You are responsible for that reality whether you actively embrace it or not.

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This is the part where you might expect some of my trademark optimism or catharsis.

Not this time. I screwed up and it wasn’t all good in the end.

It happens.

This is just one example of a million ways this can unfold.

About nine years ago, I found myself bombarding Air Force Chief of Staff Gen. Mark Welsh over a particular leadership failure.

He had committed to a former squadron commander who had been wrongly removed from his position that he would ensure a proper investigation into the matter.

Seven months later, that officer received a note stating the issue was closed without investigation. Welsh had not followed through. He deserved all my criticism and then some.

But the example I’ve just shared about my own failure wasn’t much different. We both committed on an issue really important to someone else and then didn’t follow through.

I will continue to critique senior leaders who demonstrate inadequate support for their people, especially when they fail to own it or see why it matters.

But I will also continue to do so with the humility that arises from regret.

Regret is OK. It flows naturally from screwing up and letting the mistake land, so it can be the source of learning and improvement.

I hope this example helps you.

TC is a former Air Force commanding officer and Amazon general manager. These days, he is an independent writer, speaker, coach, and consultant with expertise in organizational leadership.